Hydrochloric Acid → 6-nitro-7-(4-oxo-4H-pyridin-1-yl)-1,4-dihydroquinoxaline-2,3-dione

HRID 1488967

Reaction equation

HRID 1488967 reaction equation
F[C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=[O:13])[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[OH:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1.[OH-].[K+].Cl>CS(C)=O>[N+:14]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[N:21]1[CH:22]=[CH:23][C:18](=[O:17])[CH:19]=[CH:20]1)[NH:9][C:8](=[O:12])[C:7](=[O:13])[NH:6]2)([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 99912306-Fluoro-7-nitro-1,4-dihydroquinoxaline-2,3-dioneHCID 178418642HCID 178418642, compound

Product 1

HCID 98611296-nitro-7-(4-oxo-4H-pyridin-1-yl)-1,4-dihydroquinoxaline-2,3-dioneYield 62.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

First, 9.007 g of 7-fluoro-6-nitro-1,4-dihydroquinoxaline-2,3-dione, 7.611 g of 4-hydroxypyridine, and 5.219 g of powdered potassium hydroxide were added to 120 ml of dry dimethylsulfoxide. The mixture was stirred at 130° C. for 2 hours in a nitrogen atmosphere. Then, 50 ml of ice water and 30 ml of 4N hydrochloric acid were added to the reaction mixture so as to make it weakly acidic (pH 3 to 4). The resultant yellow precipitate was filtered and washed with water. The precipitate was dissolved by heating in a mixture containing 560 ml of water and 56 ml of conc. aqueous ammonia. One gram of activated carbon was added to the resultant mixture, stirred, and filtered. The filtrate was neutralized with conc. hydrochloric acid and ice-cooled. The precipitated crystals were then filtered and washed with water, methanol, and ethanol, successively. The resultant crystals were dried to give 7.56 g of 6-nitro-7-(4-oxo-4H-pyridin-1-yl)-1,4-dihydroquinoxaline-2,3-dione (hereinafter, abbreviated as Ia).

Workup

  1. filtrationThe resultant yellow precipitate was filtered
  2. washwashed with water
  3. dissolutionThe precipitate was dissolved
  4. temperatureby heating in a mixture
  5. additioncontaining 560 ml of water and 56 ml of conc. aqueous ammonia
  6. additionOne gram of activated carbon was added to the resultant mixture
  7. stirringstirred
  8. filtrationfiltered
  9. temperaturecooled
  10. filtrationThe precipitated crystals were then filtered
  11. washwashed with water, methanol, and ethanol
  12. customThe resultant crystals were dried

Sources & evidence

ORD record
ord-08ff0463da474729a90d3320dd332b50
Source dataset
uspto-grants-1997_10
Patent number
US05677305

Linked notes

Loading…